Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine Nitroxide Radical via Combined Iterative Nucleophilic Additions and Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones

• Published in: Journal of organic chemistry Vol. 77; no. 23; pp. 10688 - 10698
• Main Authors: Morozov, Denis A., Kirilyuk, Igor A., Komarov, Denis A., Goti, Andrea, Bagryanskaya, Irina Yu, Kuratieva, Natalia V., Grigor'ev, Igor A.
• Format: Journal Article
• Language: English
• Published: WASHINGTON Amer Chemical Soc 07.12.2012; American Chemical Society
• Subjects: Chemistry; Chemistry, Organic; cycloaddition reactions; Lewis bases; moieties; organic chemistry; oxidation; Physical Sciences; Science & Technology; stereoselectivity; STABLE FREE-RADICALS; REGIOSELECTIVE OXIDATION; ISOXAZOLIDINES; X=Y-ZH SYSTEMS; DIASTEREOSELECTIVE SYNTHESIS; REDUCTION; POTENTIAL 1,3-DIPOLES; STEREOSELECTIVE-SYNTHESIS; N-OXIDES; EN-ROUTE

A sterically hindered bis-spirocyclic C-2-symmetric chiral pyrrolidine-type nitroxide has been successfully synthesized starting from an L-tartaric derived nitrone. Starting from a pyrrolidine flanked by two methylene groups, complete quaternization of the two alpha-carbon atoms has been accomplishe...